Welcome to the Frequent Death Club
by sudoku
Summary: Dean couldn't sleep and found out that the good Doctor couldn't sleep either. They found out they had more similarities than they initially thought including their multiple deaths. Part 2 of "The Sorcerer and Team Free Will" series. Now include Tree Gelbman and the events in "Happy Death Day" and "Happy Death Day 2U".
1. Chapter 1

-Not a native speaker and not betaed so please kindly point out any mistakes  
-Warning: language, very mild spoilers up to Season 13 of Supernatural

* * *

Dean couldn't sleep. After tossing and turning for what felt like the 750th time, he finally gave up. He read drinking milk could help with insomnia. He would call Sam a nerd for knowing such things because that boy practically inhaled the contents of books. He was no nerd, he occasionally (OK, often when noone was looking) read things that were not graphic novels or what Sam rudely called comics.

He heard some light breathing in the common area. He wondered who could have infiltrated the bunker. He pulled out his gun. Nowadays, he always carried at least three weapons with him even in his sleep. You couldn't be too careful.

He peeked from the doorway to find who the intruder was. It was just Strange floating in lotus position in the middle of the room. Dean rubbed his eyes and opened them again. Yup, definitely floating. He hadn't imagined it. He was surprised that he was still capable of being surprised.

He came in to stare at his guest. He wondered whether Strange was capable of floating by himself or whether it was because of his Cloak. Yes, he capitalized the Cloak because how cool was that to own a Cloak that floated and could punch him and Sam repeatedly? It took all their skills to manage to subdue her. He knew Sam was worried that he would hate the Cloak but he actually had a mad respect for the Cloak.. She was super loyal to Strange too. He wondered what made Strange so special.

The Cloak's collars turned to look at Dean. Yeah, that was the impression Dean got and he was not going to argue with his own mind. He knew arguing with yourself was not healthy. Look at Gollum and Smeagol. The Cloak didn't see him as a threat so she continued to rest on Strange. Strange himself didn't seem to be disturbed by his presence so either he was too deep in his meditation or he could easily ignore external things when he meditated.

He shrugged and chose to sit down to stare at his guest. He and Sam just met, well, more like knocked Strange out two days ago. After settling their misunderstanding, Strange collapsed due to exhaustion, totally not because of the concussion caused by him by hitting his super thin skull with a chair. Strange insisted on going back home but Dean could see that he was still unsteady on his feet and terribly pale. Besides the doctor and Sam could totally geeked out together.

Until yesterday, he couldn't believe there was someone who could inhale more books than Sam. He also thought that they needed new friends or allies who were not hunters, sheriffs, supernatural creatures, or the son of archangel. As far as he knew, Strange was 100% human hence the super thin skull. He also didn't have any friend who was a doctor and a sorcerer before.

Strange looked impeccable in his robe. Besides his fringe, there was not a hair out of place which was totally unfair as it was 2.15 am. Dean admitted that he rocked the goatee and the robe. Not many people could pull that look without looking like a douche. Well, Bobby and Dad could also probably pull that look but no one else.

There was no way this guy had no flaws. So he stood up and examined the guy closer. He then noticed that his hands were trembling. At first he thought it was the side effects of meditation but he then remembered that his hands were shaking too when they gave him a cup of tea. No wonder that guy could connect with Sam, they drank tea and liked to eat vegan too. At first he thought the tremors were due to concussion but now he had the time to examine closer and noticed there were thick scars decorating the doctor's hands. Dean felt a stab of pity at the doctor. Sam told him about his accident and then he disappeared from the news but he never connected the dots. Well, to be fair, Strange hung out with Sam the whole day exchanging knowledge while Dean just made sure they both ate and had enough rest.

He then noticed the dark circles under the doctor's eyes. It seemed the doctor had chronic insomnia.

There were also some old cuts and bruises decorating his face. He wondered why Strange didn't use any spells to heal them.

Strange still didn't move so he went to fetch two glasses of milk and sat down watching the doctor.

After what felt like an aeon, Strange finally opened his eyes. "Thanks for not disturbing my meditation." He uncrossed his legs, smoothly landed on his two feet, and sat down opposite Dean. The Cloak swooshed behind him.

Dean shrugged. "It's not about you. I don't want to get pulled into another dimension or some shit like that."

Strange nodded. "That's right. It's never about me. But if you really disturbed my meditation, nothing bad would happen to you. I wouldn't do anything that would endanger others."

"But you would not hesitate to do things that would endanger yourself."

Strange looked stunned and remained quiet.

"There is no judgement here, at least not from me. My brother and I are the same. I think our brains are wired differently from normal people. But normal is overrated. Here is a glass of milk for you. It might help your insomnia." He pushed the glass toward Strange.

Strange cast his eyes downward. "I don't have insomnia."

"I think the dark circles under your eyes and meditating at 2 am say otherwise."

"It's not that I couldn't sleep. I could fall asleep easily. It's just hard to remain asleep with the nightmares."

Dean and Sam knew very well about nightmares. Those could be bitches. "Do you want to share with the class?"

"I don't want to burden you with such things. If you can't sleep, I can use a spell to help you with that."

"Why didn't you help yourself with the spell then?"

"It's different for me. If I sleep normally, then the normal nightmares will haunt me. If I use the spell to sleep and forget to use another protection spell, then Nightmare will haunt me. The spell to stave Nightmare off usually takes a lot from me and currently I don't have the strength for that."

Dean was thankful that he didn't mention the concussion. "Did you just say Nightmare like it is an entity?"

"Yes."

"What's that?"

"It's a Fear Lord that feasts upon people's nightmares. He has considered me to be his arch nemesis so he will always target me when I'm unaware."

Dean's eyebrows shot up to his hairline. "Arch nemesis? Do people still have those things? You speak like a graphic novel character. Why don't you kill him if he bothers you so much?"

"Well, first, he is a super powerful being. I'm already considered lucky to be able to defeat him in his own realm. I killed him, I would upset the balance of the universe because people need to have nightmares and good dreams. Thirdly, I really try not to kill if I can. Actually that should be the first." He picked the glass of milk and drank it a little bit before putting it down. Dean tried not to stare at the tremors. "This is good. Thank you."

"You're welcome. It must be hard trying not to kill. Do you know what our family motto is?"

"Your family has a motto and you laughed at me for having arch nemeses?!"

"Do you have more than one arch nemesis?"

"Don't change the subject."

Dean shrugged. "It's just what Dad used to say. Saving people. Hunting things. The Family Business. So we killed supernatural creatures that harm people. I used to kill even those who don't kill people but now we notice there are some supernatural creatures who actually don't kill. But the Nightmare! It was you who changed the subject."

"It's hard to explain about Nightmare. But as long as he doesn't get greedy and trap people in his realm, I have to let him operate for the balance of the universe."

"It must be hard trying not to kill, keeping the balance of the universe, and also protect this realm from multidimensional threats."

Strange shrugged gracefully (as if there was something that he wouldn't do gracefully Dean grumbled). "Well, not as hard as saving the world for how many times now? Thirteen times?"

Dean waved his right hand. "Apocalypse and world ending comes and goes. I honestly lost count. I guess Sammy actually counts them. So can you tell me about your regular nightmares if you don't want to tell me about the Nightmare?"

"I think you should really go to sleep. I really can help you with that."

"Strange, don't change the subject again. Why don't you want to tell me about the nightmares?"

"I don't want your pity. Besides, I've researched a lot of books. I've asked other sorcerers to help but they can't. Not with my eidetic memory."

"You have an eidetic memory. That's so unfair. And you are a doctor and a sorcerer too. We need to do some scams in order to live. Our belongings could fit inside the trunk of our Impala."

Strange smiled. "If it makes you feel any better, I don't have any money either. Our jobs don't get any pay. The place I'm staying right now in New York sort of comes with my job description. At least you don't have to keep battling interdimensional threats to earn your keep. From what I understand, you sort of inherited this bunker."

"Finders, keepers. Something like that. You changed the subject again. Why won't your eidetic memory help you with your nightmares? Are you telling me your nightmares are things that really happened to you before?"

"Yes. You're incredibly sharp for people who hit first and untie later."

"I already said I'm sorry. You know that keep delaying to tell me about your nightmares would make me more curious, right? So spill. If it's too naughty, I won't tell Sam."

"It's nothing like that. It's just that I've died many times in so many different ways and I can't make myself to forget them with my eidetic memory. Some spells could remove that particular set of memory but it will delete most of my memory too because apparently with my brain I can't just pick and choose which memory to delete."

"Hang on? Did you say you died many times?" His curiosity certainly piqued.

"Yes, I got better. Why would I lie about something like that?"

Dean chuckled. "No, I totally believe you. Sam and I have died many times too. I think mine is around 117 give or take because sometime even I'm not sure whether I can be considered dead. Sam's is around 9 give or take. How many is yours?"

"I lost count after a thousand times," The doctor said quietly. The Cloak seemed to notice its owner's distress and started to massage his shoulders.

Dean wished he had such a Cloak himself but if it came with more than 1000 deaths perhaps the cost was too high. "I'm sorry I asked. It seems to be a painful subject to you. I don't remember my first one hundred deaths but Sam remembered them all too well. I remember the rest of them but they are not within short spans, sometime years apart, so I sort of shrug them off nowadays. But yours seem to be different cases from you don't want to tell me as they're too painful, that's fine. I'm sorry I asked."

Strange shook his head. "Not your fault. I'll still have nightmares even if I don't want to talk about it. If I tell you mine, will you tell me yours?"

"Yup."

Strange then told him about the Dark Dimension, Dormammu, Kaecillius, and the zealots. How Dormammu would absorb Earth to the Dark Dimension until Strange using his own deaths to bargain with that guy (loosely speaking). The deaths varied from quick horrible deaths and slow painful deaths. Finally that guy got bored of killing Strange, let Strange returned to Earth, and promised not to disturb Earth again.

Now Dean knew why the Cloak chose the doctor. He was worthy indeed. It was one thing for him and Sam to die to save the world but it was totally another thing to let himself be slaughtered so many times like a sacrificial lamb until the maniac got bored. He now felt bad for hitting Strange's head and interrogated him after what he went through. He would make it up somehow.

He in turn told Strange about the Trickster who was not a Trickster but an archangel. He raised his eyebrows when Strange interrupted with "You know a Loki too?!" but since the doctor didn't expand on that so he continued his tales. It was the Winchesters' adventures in the last 13 years but he only told the part when they died because if he told Strange their whole adventures it would take him at least three weeks.

"See, Strange, I know you're special because you choose to die bazillion times to save the world but you've come the right people who get you. Welcome to the _Frequent Death Club_! The more times you die, the more points you will accumulate. I think you're winning at this moment. I should ask Castiel and Jack to join too. We totally should have our own T-shirts."

His freakishy tall brother chose that moment to walk in. "What T-shirts? Dean, please stop bothering Stephen. He needs his rest after his concussion."

So it was Stephen for Sam now. They must've bonded. But he felt he had formed a bond with Strange too with their early morning conversation. It was confirmed when Strange winked at him and turned to Sam. "Dean has been too kind. He kept me company when I couldn't sleep. And I totally would wear the T-shirt!"

Sam looked at his brother and then his guest. "It seems that I've missed something big."

Dean smirked. "You have no idea. What's the odd to meet a frequent death flyer?"

* * *

 **Notes:**

-Dean and Sam's number of death came from here: supernaturalwiki dot com/index dot php?title=Dead...or_are_they%3F  
-I've made a new series for more SPN and Doctor Strange's crossover when I have more ideas, I'll add to this series.  
-Please tell me what you think about this story. Not so sure about Dean's characterization here. I know he said no chick flick moment but he cared a lot about others.


	2. A new member?

-Unbetaed and not a native speaker so please kindly point out any mistakes  
-This is a sequel noone asked for but was written anyway.  
-Warnings: Language, some slight spoilers for Supernatural and vague spoilers about "Happy Death Day" and "Happy Death Day 2U". Whatever events mentioned in "Happy Death Day" are in the synopsis of the movies so that's why I said vague.  
-Sam was conveniently doing some research so he wasn't in the conversation.

* * *

"Stephen, pack your bag. We're going for a trip."

"Where're we going?"

"Louisiana."

"I can always open a portal."

Dean scratched his head. "I'll never get used to the idea that you can do that."

Stephen smiled. "Neither did I. It took me a while to learn it properly. I was a slow learner."

"That isn't what Sam said."

Stephen beamed. The old him would just agree because of course he was smart. The current him tried to appreciate others more. Sam was super smart so the compliment meant something. "He might exaggerate." He couldn't wipe the smile out of his face.

Dean snorted "Trust me. He isn't the type. I have no time for false modesty. We need to get to her ASAP."

Stephen was alarmed. "Is she in any danger from any monster? We must hurry then. Just give me the picture of the location."

"From what I heard, she could take care of herself really well. I just don't want her accidentally helping the wrong people That machine should be destroyed."

"What people and what machine?"

"Our government and the quantum thingy machine that created a time loop."

"I think my concussion from being hit by your chair hasn't healed because none of what you said makes sense."

"It is not _my_ chair. Gee, you do hold grudges. Anyway, Death told me that there was this girl who kept dying on her birthday. She..."

"Death as in an entity?!"

"Yes, yes, Death. You know Nightmare so Death is certainly not out of the question. The one with the scythe on the tarot card. Except, it's a she and she was a reaper. Then I killed her old boss, the previous Death. Not truly my fault, I didn't know he could die. To cut a long story short, she got promoted."

"Did you kill him with a chair too?"

"No, with a scythe. His scythe in fact. Just drop the chair."

"You _did_. On my head."

Dean sighed. "Do you want me to explain about the girl?"

"I still can't get around the idea that you knew Death, killed him, and befriended the new Death."

"Billie is not really my friend."

"You're on a first name basis with Death?!"

"That's her only name. Could we get back to Tree?"

"What tree?"

Dean rubbed his face tiredly. "I don't think I've explained this properly."

"You don't say."

Dean fired out his laptop. "Since you can save our travelling time by portal, I have the time to brief you about Tree Gelbman. Please don't ask me about Death anymore because it's not our current priority and frankly, it's another can of worms. Death told me about Tree and I asked a friend to do some digging."

Stephen read the email. He raised his eyebrows. Apparently the Hunters had their own networks and they kept track of anything strange (pun intended) supernatural or not.

There was a girl called Theresa Gelbman. How she got the nickname Tree was not in the email. She was a sorority girl in Bayfield University. One night on her birthday, she got killed. But she woke up in the same place and time on her birthday morning whenever she got killed. Stephen grimaced. He knew the feeling.

She kept looping and dying until she could find out who her killer was and stopped dying. Apparently the loop was caused by an experiment by Tree's boyfriend's roommate. Later, there was a mishap so the poor girl got thrown into another dimension where she needed to loop through her birthday and death all over again. Stephen could totally understand that. First introduction to the multiverse could be rough.

Dean's concern was that DARPA was interested in the research and Tree might help them because she had no idea what the government was capable of.

Stephen could see why Dean said Tree could take care of herself. The girl looked pretty bad ass and most certainly could kick his ass if he didn't have any also had an enormous respect for her. It was not easy to know that you were going to die but kept on living knowing you would end up dying anyway. In the alternate universe, she needed to kill herself so many times because she would rather put her own life in her own hands quite literally rather than lettings others die or getting murdered repeatedly. Like Stephen, she had faced deaths (metaphorically, they couldn't all be Dean who had met the literal Death) multiple times and came out a better person.

He stood up and started to take out his sling ring. "Let's meet Ms Gelbman then."

Dean nodded enthusiastically. "I have a feeling she'd prefer to be called Tree. Do you think what I'm thinking?"

"No, and I prefer not to do telepathy."

Dean grinned so widely. "A new member for the Frequent Death Club."

Sam's yell could be heard from a few doors away. "Dean, NO! Remember the Winchester's luck."

* * *

 **Notes:**

-As cool as it's to see them meet, I have no idea to write it so I need to stop it right here.  
-When I watched "Happy Death Day", I didn't expect to like it but Jessica Rothe really carried the movie. IMHO, the sequel is equally good and has more hearts.  
-Positive criticism and feedbacks are welcome.


End file.
